EP3115437B1 - Liquid crystal display device and liquid crystal composition - Google Patents
Liquid crystal display device and liquid crystal composition Download PDFInfo
- Publication number
- EP3115437B1 EP3115437B1 EP15758956.5A EP15758956A EP3115437B1 EP 3115437 B1 EP3115437 B1 EP 3115437B1 EP 15758956 A EP15758956 A EP 15758956A EP 3115437 B1 EP3115437 B1 EP 3115437B1
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- EP
- European Patent Office
- Prior art keywords
- liquid crystal
- carbons
- compound
- composition
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims description 167
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 125
- 150000001875 compounds Chemical class 0.000 claims description 232
- -1 1,4-phenylene, 1,4-phenylene Chemical group 0.000 claims description 82
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 239000000758 substrate Substances 0.000 claims description 24
- 230000003287 optical effect Effects 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 5
- 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims description 5
- 125000005453 2,5-difluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C(F)=C([H])C([*:2])=C1F 0.000 claims description 3
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
- 230000003247 decreasing effect Effects 0.000 description 25
- 238000005259 measurement Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- 230000001965 increasing effect Effects 0.000 description 18
- 239000000654 additive Substances 0.000 description 15
- 239000010408 film Substances 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 14
- 239000011521 glass Substances 0.000 description 13
- 125000002947 alkylene group Chemical group 0.000 description 12
- 230000000996 additive effect Effects 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 230000004044 response Effects 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- 0 *C(CC1)CCC1c(ccc(*)c1F)c1F Chemical compound *C(CC1)CCC1c(ccc(*)c1F)c1F 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 230000003078 antioxidant effect Effects 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- 238000002834 transmittance Methods 0.000 description 7
- 239000002518 antifoaming agent Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 230000002459 sustained effect Effects 0.000 description 6
- 229940124543 ultraviolet light absorber Drugs 0.000 description 6
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- AQAGCHUHSHTBLP-AFBJXSTISA-N (4z,8z,13z)-11-hexyl-1-oxacyclopentadeca-4,8,13-trien-2-one Chemical compound CCCCCCC1C\C=C/CC\C=C/CC(=O)OC\C=C/C1 AQAGCHUHSHTBLP-AFBJXSTISA-N 0.000 description 4
- 125000006017 1-propenyl group Chemical group 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 3
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000006039 1-hexenyl group Chemical group 0.000 description 2
- 125000006023 1-pentenyl group Chemical group 0.000 description 2
- 125000005450 2,3-difluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C(F)=C(F)C([*:1])=C1[H] 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000005734 2-chloro-3-fluoro-1,4-phenylene group Chemical group [H]C1=C([H])C([*:1])=C(Cl)C(F)=C1[*:2] 0.000 description 2
- 125000006040 2-hexenyl group Chemical group 0.000 description 2
- 125000006024 2-pentenyl group Chemical group 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- 125000006041 3-hexenyl group Chemical group 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000005742 alkyl ethenyl group Chemical group 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000013213 extrapolation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- ZKJNETINGMOHJG-UHFFFAOYSA-N 1-prop-1-enoxyprop-1-ene Chemical class CC=COC=CC ZKJNETINGMOHJG-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 description 1
- 125000005732 2,6-difluoro-1,4-phenylene group Chemical group [H]C1=C(F)C([*:1])=C(F)C([H])=C1[*:2] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000011903 deuterated solvents Substances 0.000 description 1
- 125000005675 difluoroethenyl group Chemical group [H]C(*)=C(F)F 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000005670 ethenylalkyl group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- HVRUGFJYCAFAAN-UHFFFAOYSA-N o-C2H5C6H4Br Natural products CCC1=CC=CC=C1Br HVRUGFJYCAFAAN-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003216 poly(methylphenylsiloxane) Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
- C09K19/0208—Twisted Nematic (T.N.); Super Twisted Nematic (S.T.N.); Optical Mode Interference (O.M.I.)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
- C09K19/0216—Super Birefringence Effect (S.B.E.); Electrically Controlled Birefringence (E.C.B.)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
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Definitions
- the invention relates to a liquid crystal display device including a liquid crystal composition having negative dielectric anisotropy and having an FFS mode.
- a classification based on an operating mode for liquid crystal molecules includes modes such as PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS (in-plane switching), VA (vertical alignment), FFS (fringe field switching) and FPA (field-induced photo-reactive alignment) .
- a classification based on a driving mode in the device includes PM (passive matrix) and AM (active matrix). The PM is classified into static, multiplex and so forth, and the AM is classified into TFT (thin film transistor), MIM (metal-insulator-metal) and so forth.
- the TFT is classified into amorphous silicon and polycrystal silicon.
- the latter is classified into a high temperature type and a low temperature type depending on the production process.
- a classification based on a light source includes a reflection type utilizing natural light, a transmission type utilizing a backlight and a semi-transmission type utilizing both natural light and a backlight.
- the liquid crystal display device includes a liquid crystal composition having a nematic phase.
- This composition has suitable characteristics.
- An AM device having good characteristics can be obtained by improving the characteristics of this composition.
- Table 1 below summarizes the relationship between these two characteristics. The characteristics of the composition will be further explained on the basis of a commercially available AM device.
- the temperature range of a nematic phase relates to the temperature range in which the device can be used.
- a desirable maximum temperature of the nematic phase is approximately 70 °C or higher and a desirable minimum temperature of the nematic phase is approximately -10 °C or lower.
- the viscosity of the composition relates to the response time of the device. A short response time is desirable for displaying moving images on the device.
- Characteristics of Compositions and AM Devices No. Characteristics of Compositions Characteristics of AM Devices 1 a wide temperature range of a nematic phase a wide temperature range in which a device can be used 2 a small viscosity a short response time 3 suitable optical anisotropy a large contrast ratio 4 a large positive or large negative dielectric anisotropy a low threshold voltage and low power consumption, a large contrast ratio 5 a large specific resistance a large voltage holding ratio and a large contrast ratio 6 a high stability to ultraviolet light and heat a long service life
- the optical anisotropy of the composition relates to the contrast ratio of the device.
- a large optical anisotropy or a small optical anisotropy, namely a suitable optical anisotropy, is necessary depending on the mode of the device.
- the product ( ⁇ n ⁇ d) of the optical anisotropy ( ⁇ n) of the composition and the cell gap (d) of the device is designed so as to maximize the contrast ratio.
- a suitable value of the product depends on the type of operating mode. This value is in the range of approximately 0.30 micrometers to approximately 0.40 micrometers for a device having a VA mode, and in the range of approximately 0.20 micrometers to approximately 0.30 micrometers for a device having an IPS mode or an FFS mode.
- a composition having a large optical anisotropy is desirable for a device having a small cell gap.
- a large dielectric anisotropy of the composition contributes to a low threshold voltage, low power consumption and a large contrast ratio of the device. A large dielectric anisotropy is thus desirable.
- a large specific resistance of the composition contributes to a large voltage holding ratio and a large contrast ratio of the device. It is thus desirable that a composition should have a large specific resistance at a temperature close to the maximum temperature of a nematic phase as well as at room temperature in the initial stages. It is desirable that a composition should have a large specific resistance at a temperature close to the maximum temperature of a nematic phase as well as at room temperature, after it has been used for a long time.
- the stability of the composition to ultraviolet light and heat relates to the service life of the device. The device has a long service life when the stability is high. Characteristics of this kind are desirable for an AM device used for a liquid crystal projector, a liquid crystal television and so forth.
- a liquid crystal composition including a polymer is used for a liquid crystal display device with a polymer sustained alignment (PSA) type.
- PSA polymer sustained alignment
- a composition to which a small amount of polymerizable compound has been added is poured into a device.
- the composition is irradiated with ultraviolet light, while a voltage is applied between the substrates of this device.
- the polymerizable compound is polymerized to give a network structure of a polymer in the composition.
- the polymer makes it possible to adjust the orientation of liquid crystal molecules, and thus the response time of the device is decreased and image burn-in is improved.
- Such effect of the polymer can be expected for a device having a mode such as TN, ECB, OCB, IPS, VA, FFS or FPA.
- a composition having positive dielectric anisotropy is used for an AM device having a TN mode.
- a composition having negative dielectric anisotropy is used for an AM device having a VA mode.
- a composition having positive or negative dielectric anisotropy is used for an AM device having an IPS mode or an FFS mode.
- a composition having positive or negative dielectric anisotropy is used for an AM device with a polymer sustained alignment type.
- a flicker sometimes is generated on a display screen when a liquid crystal display device is used for a long time.
- the flicker relates to image burn-in, and it is estimated that the flicker is caused by the difference between electric potential of the positive frame and the negative frame when the device is driven by an alternating current.
- An improvement has been tried in order to suppress the generation of the flicker in view of the structure of the device or the component of the composition.
- Patent document No. 1 WO 2010-131594 A .
- JP H02-64525 A aims at reducing a flicker of a display panel by providing an orienting film on the surface of a display transparent electrode part and equalizing the thickness of the orienting film of an array substrate to that of the material of the orienting film on the side of a counter electrode substrate.
- JP 2000-275645 A aims at decreasing uneven distribution of charges in the thickness direction of a liquid crystal layer and at suppressing generation of flickers by forming first and second alignment films, having different characteristics from each other in such a manner that the DC voltage remaining between the first alignment film and the second alignment film after AC voltage is applied between the first and second electrodes is smaller than the DC voltage to remain, when the characteristics of the films are made equal.
- JP 2008-134291 A teaches that the luminance of a backlight BL is switched into three or more levels by a backlight controlling circuit CNT.
- a frame frequency rendering a flicker rate into zero is selected according to the switched luminance level by a first table memory.
- a drive clock at a frequency corresponding to the frame frequency is generated by an oscillator, and a display panel is driven based on the drive clock.
- WO 2014/024648 A1 relates to a liquid crystal composition containing a compound having three or more polymerizable groups as a first component and a compound having one or two polymerizable groups as a second component, and optionally containing a specific compound having a large negative dielectric anisotropy and low lower limit temperature as a third component or a specific compound having a low viscosity or high upper limit temperature as a fourth component; and a liquid crystal display element containing this composition.
- WO 2014/006963 A1 relates to a liquid crystal composition containing compound (1) and compound (2), and a liquid crystal display element containing said composition.
- P1 and P2 represent polymerizable groups
- rings A, B, C, and E represent a 1,4-cyclohexylene, a 1,4-phenylene and such
- ring D represent a 2,3-difluoro-1,4-phenylene and such
- Z1 and Z2 represent an alkylene and such
- L1, Z3 and Z4 represent a single bond and such
- R1 and R2 represent an alkyl and such
- q, r and s represent the number 1 and such.
- WO 2013/175892 A1 relates to a liquid crystal composition having a negative dielectric anisotropy and a ratio of the rotational viscosity to the elastic constant of 4.2 GPa.s/N or less, and containing a specific compound that has a large negative dielectric anisotropy as a first component and a specific compound that has a polymerizable group as a second component.
- the aim of the invention is to provide a liquid crystal display device that has characteristics such as a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, a long service life and a small flicker rate.
- the liquid crystal composition comprised in the liquid crystal display device satisfies at least one of characteristics such as a high maximum temperature of a nematic phase, a low minimum temperature of a nematic phase, a small viscosity, a suitable optical anisotropy, a large negative dielectric anisotropy, a large specific resistance, a high stability to ultraviolet light and a high stability to heat.
- the liquid crystal composition is suitably balanced between at least two of the characteristics.
- the invention relates to a liquid crystal display device as defined by claim 1. Preferred embodiments are depicted in the dependent claims.
- One of the advantages of the invention is to provide a liquid crystal display device that has characteristics such as a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, a long service life and a small flicker rate.
- the liquid crystal composition comprised in the liquid crystal display device has the advantage to satisfy at least one of characteristics such as a high maximum temperature of a nematic phase, a low minimum temperature of a nematic phase, a small viscosity, a suitable optical anisotropy, a large negative dielectric anisotropy, a large specific resistance, a high stability to ultraviolet light and a high stability to heat.
- the liquid crystal composition is suitably balanced between at least two of the characteristics.
- Liquid crystal composition and “liquid crystal display device” are sometimes abbreviated to “composition” and “device,” respectively.
- “Liquid crystal display device” is a generic term for a liquid crystal display panel and a liquid crystal display module.
- Liquid crystal compound is a generic term for a compound having a liquid crystal phase such as a nematic phase or a smectic phase, and for a compound having no liquid crystal phases but being mixed to a composition for the purpose of adjusting the characteristics, such as the temperature range of a nematic phase, the viscosity and the dielectric anisotropy.
- This compound has a six-membered ring such as 1,4-cyclohexylene or 1,4-phenylene, and its molecular structure is rod-like.
- Polymerizable compound is a compound that is added to a composition in order to form a polymer in it.
- a liquid crystal composition is prepared by mixing a plurality of liquid crystal compounds.
- the ratio of a liquid crystal compound (content) is expressed as a percentage by weight (% by weight) based on the weight of this composition.
- An additive such as an optically active compound, an antioxidant, an ultraviolet light absorber, a coloring matter, an antifoaming agent, a polymerizable compound, a polymerization initiator and a polymerization inhibitor is added to this composition as required.
- the ratio of the additive (added amount) is expressed as a percentage by weight (% by weight) based on the weight of the liquid crystal composition in the same manner as with the liquid crystal compound. Weight parts per million (ppm) is sometimes used.
- the ratio of the polymerization initiator and the polymerization inhibitor is exceptionally expressed on the basis of the weight of the polymerizable compound.
- a higher limit of the temperature range of a nematic phase is sometimes abbreviated to "the maximum temperature.”
- “A lower limit of the temperature range of a nematic phase” is sometimes abbreviated to “the minimum temperature.” That "specific resistance is large” means that a composition has a large specific resistance at a temperature close to the maximum temperature of a nematic phase as well as at room temperature in the initial stages, and that the composition has a large specific resistance at a temperature close to the maximum temperature of a nematic phase as well as at room temperature, after it has been used for a long time.
- That "a voltage holding ratio is large” means that a device has a large voltage holding ratio at a temperature close to the maximum temperature of a nematic phase as well as at room temperature in the initial stages, and that the device has a large voltage holding ratio at a temperature close to the maximum temperature of a nematic phase as well as at room temperature, after it has been used for a long time.
- the expression “increase the dielectric anisotropy” means that its value increases positively when the composition has positive dielectric anisotropy, and that its value increases negatively when the composition has negative dielectric anisotropy.
- At least one 'A' means that the number of 'A' is arbitrary.
- the expression "at least one 'A' may be replaced by 'B'” means that the position of 'A' is arbitrary when the number of 'A' is one. The positions can also be selected without restriction when the number of 'A' is two or more.
- the expression "in the alkyl, at least one -CH 2 - may be replaced by -O- or -S-" includes groups such as -OCH 3 , -CH 2 OCH 3 , -CH 2 OCH 2 CH 2 OCH 3 , -SCH 2 CH 2 CH 3 , -CH 2 CH 2 SCH 3 and -CH 2 OCH 2 CH 2 SCH 3 .
- -CH 2 - of a methyl moiety (-CH 2 -H) in alkyl and so forth should be replaced by -O- to give -O-H.
- the symbol such as A, B or F surrounded by a hexagon corresponds to ring A, ring B or ring F, respectively.
- the hexagon represents a six-membered ring or a condensed ring.
- an oblique line crossing the hexagon of ring F means that the binding position of a P 1 -Sp 1 group on the ring can be arbitrarily selected.
- the same rule applies to a P 2 -Sp 2 group on ring G or the like.
- a subscript such as "a” shows the number of a group bonded to a ring such as ring F. Two P 1 -Sp 1 groups are present on ring F when "a" is 2.
- Two groups represented by two P 1 -Sp 1 groups may be the same or different. The same rule applies to arbitrary two when "a” is greater than 2. The same rule also applies to another group.
- a compound represented by formula (1) is sometimes abbreviated to "compound (1).” This abbreviation applies to a compound represented by formula (2) or the like.
- Compound (1) means one compound, a mixture of two compounds or a mixture of three or more compounds represented by formula (1).
- R 1 is used for a plurality of compounds in the chemical formulas of component compounds.
- two groups represented by two arbitrary R 1 may be the same or different.
- R 1 of compound (1-1) is ethyl and R 1 of compound (1-2) is ethyl.
- R 1 of compound (1-1) is ethyl and R 1 of compound (1-2) is propyl.
- the same rule applies to symbols such as another terminal group.
- two of ring A are present when m is 2.
- two groups represented by two of ring A may be the same or different.
- the same rule applies to arbitrary two of ring A, when m is greater than 2.
- the same rule also applies to symbols such as Z 1 and ring B.
- 2-Fluoro-1,4-phenylene means the two divalent groups described below. Fluorine may be facing left (L) or facing right (R) in a chemical formula. The same rule also applies to an asymmetric divalent group formed from a ring by removing two hydrogens, such as tetrahydropyran-2,5-diyl.
- the invention includes the following items.
- the description also includes the following items.
- a transmission-type device including the composition described above and a polymerizable compound in this composition is polymerized.
- the invention also includes the following items.
- the liquid crystal display device including the liquid crystal composition described above, wherein the liquid crystal composition includes at least one compound selected from the group of compounds represented by formula (1-1) to formula (1-20) as the first component, and the total weight of compounds represented by formula (1-1), formula (1-2), formula (1-3), formula (1-5), formula (1-7), formula (1-8), formula (1-10), formula (1-14), formula (1-17) and formula (1-18) is in the range of 50% by weight to 100% by weight based on the weight of the first component.
- the liquid crystal display device of the invention includes a first substrate, a second substrate and a liquid crystal composition having a nematic phase that is placed between these substrates, wherein the flicker rate of the liquid crystal display device is in the range of 0% to 1%.
- the flicker rate (%) is expressed by [
- the flicker relates to image burn-in, and it is estimated that the flicker is caused by the difference between electric potential of the positive frame and the negative frame when the device is driven by an alternating current.
- the generation of the flicker can be suppressed by suitably selecting the component of the composition included in the device.
- composition of the invention The composition used in the invention (hereinafter also referred to as composition of the invention) will be explained in the following order: First, the constitution of component compounds in the composition will be explained. Second, the main characteristics of the component compounds and the main effects of these compounds on the composition will be explained. Third, a combination of the components in the composition, a desirable ratio of the components and its basis will be explained. Fourth, a desirable embodiment of the component compounds will be explained. Fifth, desirable component compounds will be shown. Sixth, additives that may be added to the composition will be explained. Seventh, methods for synthesizing the component compounds will be explained. Last, the use of the composition will be explained.
- compositions of the invention are classified into composition A and composition B.
- Composition A may further include any other liquid crystal compound, an additive and so forth, in addition to liquid crystal compounds selected from compound (1) and compound (2).
- Any other liquid crystal compound is a liquid crystal compound that is different from compound (1) and compound (2).
- Such a compound is mixed with the composition for the purpose of further adjusting the characteristics.
- the additive includes an optically active compound, an antioxidant, an ultraviolet light absorber, a coloring matter, an antifoaming agent, a polymerizable compound, a polymerization initiator and a polymerization inhibitor.
- Composition B consists essentially of liquid crystal compounds selected from compound (1) and compound (2).
- the term "essentially” means that the composition may include an additive, but does not include any other liquid crystal compound.
- Composition B has a smaller number of components than composition A.
- Composition B is preferable to composition A in view of cost reduction.
- Composition A is preferable to composition B in view of the fact that characteristics can be further adjusted by mixing with any other liquid crystal compound.
- Table 2 summarizes the main characteristics of the component compounds based on the effects of the invention.
- the symbol L stands for "large” or “high”
- the symbol M stands for “medium”
- the symbol S stands for "small” or “low.”
- the symbols L, M and S mean a classification based on a qualitative comparison among the component compounds, and the symbol 0 means that the value is zero or close to zero. Table 2.
- Compound (1) increases the dielectric anisotropy, and decreases the minimum temperature.
- Compound (2) decreases the viscosity or increases the maximum temperature.
- Compound (3) gives a polymer by polymerization, and this polymer decreases the response time of a device, and improves image burn-in.
- a combination of the components in the composition is the first and second components, the first and additive components or the first, second and additive components.
- a desirable combination of the components is the first and second components or the first, second and additive components.
- a desirable ratio of the first component is approximately 20% by weight or more for increasing the dielectric anisotropy, and approximately 95% by weight or less for decreasing the minimum temperature.
- a more desirable ratio is in the range of approximately 25% by weight to approximately 80% by weight.
- An especially desirable ratio is in the range of approximately 30% by weight to approximately 75% by weight.
- a desirable ratio of the second component is approximately 5% by weight or more for increasing the maximum temperature or for decreasing the viscosity, and approximately 80% by weight or less for increasing the dielectric anisotropy.
- a more desirable ratio is in the range of approximately 20% by weight to approximately 75% by weight.
- An especially desirable ratio is in the range of approximately 25% by weight to approximately 70% by weight.
- Compound (3) is added to the composition for adjusting to a reference device with a polymer sustained alignment type according to the description.
- a desirable ratio of the additive is approximately 0.03% by weight or more for orienting liquid crystal molecules, and approximately 10% by weight or less for preventing a poor display of a device.
- a more desirable ratio is in the range of approximately 0.1% by weight to approximately 2% by weight.
- An especially desirable ratio is in the range of approximately 0.2% by weight to approximately 1% by weight.
- R 1 and R 2 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkenyloxy having 2 to 12 carbons or alkyl having 1 to 12 carbons in which at least one hydrogen has been replaced by halogen.
- Desirable R 1 or R 2 is alkyl having 1 to 12 carbons for increasing the stability, and alkoxy having 1 to 12 carbons for increasing the dielectric anisotropy.
- R 3 and R 4 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkyl having 1 to 12 carbons in which at least one hydrogen has been replaced by halogen or alkenyl having 2 to 12 carbons in which at least one hydrogen has been replaced by halogen.
- Desirable R 3 or R 4 is alkenyl having 2 to 12 carbons for decreasing the viscosity, and alkyl having 1 to 12 carbons for increasing the stability.
- the alkyl is straight-chain or branched-chain, and does not include cycloalkyl.
- Straight-chain alkyl is preferable to branched-chain alkyl.
- Halogen means fluorine, chlorine, bromine and iodine. Desirable halogen is fluorine and chlorine. More desirable halogen is fluorine.
- Desirable alkyl is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl. More desirable alkyl is ethyl, propyl, butyl, pentyl or heptyl for decreasing the viscosity.
- Desirable alkoxy is methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy or heptyloxy. More desirable alkoxy is methoxy or ethoxy for decreasing the viscosity.
- Desirable alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl or 5-hexenyl. More desirable alkenyl is vinyl, 1-propenyl, 3-butenyl or 3-pentenyl for decreasing the viscosity.
- Trans is preferable in the alkenyl such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyl and 3-hexenyl for decreasing the viscosity.
- Cis is preferable in the alkenyl such as 2-butenyl, 2-pentenyl and 2-hexenyl.
- Desirable alkenyloxy is vinyloxy, allyloxy, 3-butenyloxy, 3-pentenyloxy or 4-pentenyloxy. More desirable alkenyloxy is allyloxy or 3-butenyloxy for decreasing the viscosity.
- alkyl in which at least one hydrogen has been replaced by halogen are fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl, 7-fluoroheptyl or 8-fluorooctyl. More desirable examples are 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl or 5-fluoropentyl for increasing the dielectric anisotropy.
- alkenyl in which at least one hydrogen has been replaced by halogen are 2,2-difluorovinyl, 3,3-difluoro-2-propenyl, 4,4-difluoro-3-butenyl, 5,5-difluoro-4-pentenyl or 6,6-difluoro-5-hexenyl. More desirable examples are 2,2-difluorovinyl or 4,4-difluoro-3-butenyl for decreasing the viscosity.
- Ring A and ring C are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine or chlorine or tetrahydropyran-2,5-diyl.
- Desirable examples of "1,4-phenylene in which at least one hydrogen has been replaced by fluorine or chlorine" are 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene or 2-chloro-3-fluoro-1,4-phenylene.
- Desirable ring A or ring C is 1,4-cyclohexylene for decreasing the viscosity, and tetrahydropyran-2,5-diyl for increasing the dielectric anisotropy, and 1,4-phenylene for increasing the optical anisotropy.
- trans is preferable to cis for increasing the maximum temperature.
- Tetrahydropyran-2,5-diyl is preferably
- Ring B is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4,5-trifluoronaphthalene-2,6-diyl or 7,8-difluorochroman-2,6-diyl.
- Desirable ring B is 2,3-difluoro-1,4-phenylene for decreasing the viscosity, and 2-chloro-3-fluoro-1,4-phenylene for decreasing the optical anisotropy, and 7,8-difluorochroman-2,6-diyl for increasing the dielectric anisotropy.
- Ring D and ring E are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene. Desirable ring D or ring E is 1,4-cyclohexylene for decreasing the viscosity or for increasing the maximum temperature, and 1,4-phenylene for decreasing the minimum temperature.
- Z 1 and Z 2 are independently a single bond, ethylene, carbonyloxy or methyleneoxy. Desirable Z 1 or Z 2 is a single bond for decreasing the viscosity, and ethylene for decreasing the minimum temperature, and methyleneoxy for increasing the dielectric anisotropy.
- Z 3 is a single bond, ethylene or carbonyloxy. Desirable Z 3 is a single bond for increasing the stability.
- m is 1, 2 or 3, n is 0 or 1, and the sum of m and n is 3 or less. Desirable m is 1 for decreasing the viscosity, and is 2 or 3 for increasing the maximum temperature. Desirable n is 0 for decreasing the viscosity, and is 1 for decreasing the minimum temperature. o is 1, 2 or 3. Desirable o is 1 for decreasing the viscosity, and 2 or 3 for increasing the maximum temperature.
- P 1 , P 2 and P 3 are a polymerizable group.
- M 1 , M 2 and M 3 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons or alkyl having 1 to 5 carbons in which at least one hydrogen has been replaced by halogen.
- Desirable alkyl is methyl, ethyl or propyl. More desirable alkyl is methyl. Desirable examples of alkyl in which at least one hydrogen has been replaced by halogen are fluoromethyl, 2-fluoroethyl or 3-fluoropropyl. More desirable examples of alkyl in which at least one hydrogen has been replaced by halogen are fluoromethyl.
- Desirable M 1 , M 2 or M 3 is hydrogen or methyl for increasing the reactivity.
- More desirable M 1 is methyl, and more desirable M 2 or M 3 is hydrogen.
- Two groups represented by arbitrary two M 1 may be the same or different when compound (3) has a plurality of polymerizable groups selected from the group of groups represented by formula (P-1) to formula (P-6). The same rule applies also to M 2 or M 3 .
- At least one of a numbers of Sp 1 and c numbers of Sp 3 is alkylene in which at least one -CH 2 - has been replaced by -O-, -COO-, -OCO- or -OCOO- when all of a numbers of P 1 and c numbers of P 3 are group (P-4). That is to say, there is no possibility that all of a numbers of P 1 and c numbers of P 3 are alkenyl such as 1-propenyl.
- Desirable Sp 1 , Sp 2 or Sp 3 is a single bond, alkylene having 1 to 10 or alkylene in which one or two -CH 2 - has been replaced by -O-, -COO- or -OCO-.
- More desirable Sp 1 , Sp 2 or Sp 3 is a single bond, alkylene having 1 to 6 or alkylene in which one -CH 2 - has been replaced by -O-.
- Especially desirable Sp 1 , Sp 2 or Sp 3 is a single bond.
- Ring F and ring H are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidine-2-yl or pyridine-2-yl, and in these rings at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkyl having 1 to 12 carbons in which at least one hydrogen has been replaced by halogen.
- Halogen means fluorine, chlorine, bromine and iodine. Desirable halogen is fluorine and chlorine. More desirable halogen is fluorine.
- Desirable ring F or ring H is phenyl, 2-fluorophenyl, 3-fluorophenyl, or 4-fluorophenyl. Desirable ring F or ring H is phenyl.
- Ring G is 1,4-cyclohexylene, 1,4-cyclohexylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl
- Desirable ring G is 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene or 2,6-difluoro-1,4-phenylene. More desirable ring G is 1,4-phenylene or 2-fluoro-1,4-phenylene. Especially desirable ring G is 1,4-phenylene. Especially desirable ring G is also 2-fluoro-1,4-phenylene.
- Desirable Z 4 or Z 5 is a single bond, -CH 2 CH 2 -, -CH 2 O-, -OCH 2 -, -COO- or -OCO-. More desirable Z 4 or Z 5 is a single bond.
- d is 0, 1 or 2. Desirable d is 0 or 1. a, b and c are independently 0, 1, 2, 3 or 4, and the sum of a, b and c is 1 or more. Desirable a, b or c is 1 or 2.
- the first component is compound (1) in which the dielectric anisotropy is negative.
- Desirable compound (1) is compound (1-1) to compound (1-20) described in item 2.
- Desirable compounds in view of suppressing the flicker are as follows. Compounds having a single bond or ethylene are preferable to compounds having methyleneoxy. Compounds having 1,4-cyclohexylene or 1,4-phenylene are preferable to compounds having tetrahydropyran-2,5-diyl. More desirable compounds are specifically compound (1-1), compound (1-2), compound (1-3), compound (1-5), compound (1-7), compound (1-8), compound (1-10), compound (1-14), compound (1-17) and compound (1-18).
- the total weight of these compounds should be in the range of 50% by weight to 100% by weight based on the weight of the first component. It is desirable that the total weight of these compounds should be in the range of 10% by weight to 80% by weight based on the weight of the liquid crystal composition. It is more desirable that the total weight of these compounds should be in the range of 20% by weight to 60% by weight based on the weight of the liquid crystal composition.
- the second component is compound (2) in which the dielectric anisotropy is zero or close to zero.
- Desirable compound (2) is compound (2-1) to compound (2-13) described in item 5.
- Desirable compound (3) is compound (3-1) to compound (3-27) described below.
- P 4 , P 5 and P 6 are independently a polymerizable group selected from the group of groups represented by formula (P-1) to formula (P-3): in formula (P-1) to formula (P-3), M 1 , M 2 and M 3 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons or alkyl having 1 to 5 carbons in which at least one hydrogen has been replaced by halogen;
- At least one of the additive component is compound (3-1), compound (3-2), compound (3-24), compound (3-25), compound (3-26) or compound (3-27). It is desirable that at least two of the additive component are a combination of compound (3-1) and compound (3-2), compound (3-1) and compound (3-18), compound (3-2) and compound (3-24), compound (3-2) and compound (3-25), compound (3-2) and compound (3-26), compound (3-25) and compound (3-26) or compound (3-18) and compound (3-24).
- M 1 , M 2 or M 3 is hydrogen or methyl.
- additives that may be added to the composition will be explained.
- Such additives include an optically active compound, an antioxidant, an ultraviolet light absorber, a coloring matter, an antifoaming agent, a polymerizable compound, a polymerization initiator and a polymerization inhibitor.
- the optically active compound is added to the composition for the purpose of inducing the helical structure of liquid crystal molecules and giving a twist angle.
- examples of such compounds include compound (4-1) to compound (4-5) .
- a desirable ratio of the optically active compound is approximately 5% by weight or less, and a more desirable ratio is in the range of approximately 0.01% by weight to approximately 2% by weight.
- the antioxidant is added to the composition in order to prevent a decrease in specific resistance that is caused by heating under air, or to maintain a large voltage holding ratio at a temperature close to the maximum temperature as well as at room temperature, after the device has been used for a long time.
- a desirable example of the antioxidant is compound (5) where n is an integer from 1 to 9, for instance.
- desirable n is 1, 3, 5, 7 or 9. More desirable n is 7.
- Compound (5) where n is 7 is effective in maintaining a large voltage holding ratio at a temperature close to the maximum temperature as well as at room temperature, after the device has been used for a long time, since it has a small volatility.
- a desirable ratio of the antioxidant is approximately 50 ppm or more for achieving its effect and is approximately 600 ppm or less for avoiding a decrease in the maximum temperature or avoiding an increase in the minimum temperature.
- a more desirable ratio is in the range of approximately 100 ppm to approximately 300 ppm.
- Desirable examples of the ultraviolet light absorber include benzophenone derivatives, benzoate derivatives and triazole derivatives.
- a light stabilizer such as an amine having steric hindrance is also desirable.
- a desirable ratio of the ultraviolet light absorber or the light stabilizer is approximately 50 ppm or more for achieving its effect and is approximately 10,000 ppm or less for avoiding a decrease in the maximum temperature or avoiding an increase in the minimum temperature. A more desirable ratio is in the range of approximately 100 ppm to approximately 10,000 ppm.
- a dichroic dye such as an azo dye or an anthraquinone dye is added to the composition for adjusting to a device having a guest host (GH) mode.
- a desirable ratio of the coloring matter is in the range of approximately 0.01% by weight to approximately 10% by weight.
- the antifoaming agent such as dimethyl silicone oil or methyl phenyl silicone oil is added to the composition for preventing foam formation.
- a desirable ratio of the antifoaming agent is approximately 1 ppm or more for achieving its effect and is approximately 1,000 ppm or less for avoiding a poor display.
- a more desirable ratio is in the range of approximately 1 ppm to approximately 500 ppm.
- the polymerizable compound is used for adjusting to a reference device with a PSA (polymer sustained alignment) type according to the description.
- Compound (3) is suitable for this purpose.
- a polymerizable compound that is different from compound (3) may be added to the composition, together with compound (3).
- Desirable examples of such a polymerizable compound include compounds such as acrylates, methacrylates, vinyl compounds, vinyloxy compounds, propenyl ethers, epoxy compounds (oxiranes, oxetanes) and vinyl ketones. More desirable examples are acrylate derivatives or methacrylate derivatives.
- a desirable ratio of compound (3) is 10% by weight or more based on the total weight of the polymerizable compound. A more desirable ratio is 50% by weight or more. An especially desirable ratio is 80% by weight or more. An especially desirable ratio is also 100% by weight.
- a polymerizable compound such as compound (3) is polymerized on irradiation with ultraviolet light. It may be polymerized in the presence of an initiator such as a photopolymerization initiator. Suitable conditions for polymerization, and a suitable type and amount of the initiator are known to a person skilled in the art, and are described in the literature. For example, Irgacure 651 (registered trademark; BASF), Irgacure 184 (registered trademark; BASF) or Darocur 1173 (registered trademark; BASF), each of which is a photoinitiator, is suitable for radical polymerization.
- a desirable ratio of the photopolymerization initiator is in the range of approximately 0.1% by weight to approximately 5% by weight based on the weight of the polymerizable compound. A more desirable ratio is in the range of approximately 1% by weight to approximately 3% by weight.
- the polymerization inhibitor may be added in order to prevent the polymerization when a polymerizable compound such as compound (3) is kept in storage.
- the polymerizable compound is usually added to the composition without removing the polymerization inhibitor.
- the polymerization inhibitor include hydroquinone derivatives such as hydroquinone and methylhydroquinone, 4-tert-butylcatechol, 4-methoxyphenol and phenothiazine.
- Compound (1-7) is prepared by the method described in JP 2000-53602 A .
- Compound (2-1) is prepared by the method described in JP S59-176221 A (1984 ).
- a compound of formula (5) where n is 1 is available from Sigma-Aldrich Corporation.
- Compound (5) where n is 7, for instance, is synthesized according to the method described in U. S. Patent No. 3,660,505 .
- the composition mainly has a minimum temperature of approximately -10 °C or lower, a maximum temperature of approximately 70 °C or higher, and an optical anisotropy in the range of approximately 0.07 to approximately 0.20.
- a composition having an optical anisotropy in the range of approximately 0.08 to approximately 0.25 may be prepared by adjusting the ratio of the component compounds or by mixing with any other liquid crystal compound.
- a composition having an optical anisotropy in the range of approximately 0.10 to approximately 0.30 may be prepared by trial and error.
- a device including this composition has a large voltage holding ratio.
- This composition is suitable for an AM device.
- This composition is suitable especially for an AM device having a transmission type.
- This composition can be used as a composition having a nematic phase and as an optically active composition by adding an optically active compound.
- the composition can be used for an AM device. It can also be used for a PM device.
- the composition can also be used for the AM device and the PM device having a mode such as PC, TN, STN, ECB, OCB, IPS, FFS, VA and FPA. It is especially desirable to use the composition for the AM device having a mode of TN, OCB, IPS or FFS.
- the orientation of liquid crystal molecules may be parallel or perpendicular to the glass substrate, when no voltage is applied.
- These devices may be of a reflection type, a transmission type or a semi-transmission type. It is desirable to use the composition for a device having the transmission type.
- the composition can be used for an amorphous silicon-TFT device or a polycrystal silicon-TFT device.
- the composition is also usable for an NCAP (nematic curvilinear aligned phase) device prepared by microcapsulating the composition, and for a PD (polymer dispersed) device in which a three-dimensional network-polymer is formed in the composition.
- the invention will be explained in more detail by way of examples. The invention is not limited to the examples.
- the invention includes a mixture of the composition in Example 1 and the composition in Example 2.
- the invention also includes a mixture prepared by mixing at least two compositions in Examples. Compounds prepared herein were identified by methods such as NMR analysis. The characteristics of the compounds, compositions and devices were measured by the methods described below.
- NMR Analysis A model DRX-500 apparatus made by Bruker BioSpin Corporation was used for measurement. In the measurement of 1 H-NMR, a sample was dissolved in a deuterated solvent such as CDCl 3 , and the measurement was carried out under the conditions of room temperature, 500 MHz and the accumulation of 16 scans. Tetramethylsilane was used as an internal standard. In the measurement of 19 F-NMR, CFCl 3 was used as the internal standard, and 24 scans were accumulated.
- the symbols s, d, t, q, quin, sex, m and br stand for a singlet, a doublet, a triplet, a quartet, a quintet, a sextet, a multiplet and line-broadening, respectively.
- a gas chromatograph Model GC-14B made by Shimadzu Corporation was used for measurement.
- the carrier gas was helium (2 milliliters per minute) .
- the sample injector and the detector (FID) were set to 280 °C and 300 °C, respectively.
- a capillary column DB-1 (length 30 meters, bore 0.32 millimeter, film thickness 0.25 micrometers, dimethylpolysiloxane as the stationary phase, non-polar) made by Agilent Technologies, Inc. was used for the separation of component compounds . After the column had been kept at 200 °C for 2 minutes, it was further heated to 280 °C at the rate of 5 °C per minute.
- a sample was dissolved in acetone (0.1% by weight), and 1 microliter of the solution was injected into the sample injector.
- a recorder used was Model C-R5A Chromatopac Integrator made by Shimadzu Corporation or its equivalent. The resulting gas chromatogram showed the retention time of peaks and the peak areas corresponding to the component compounds.
- Solvents for diluting the sample may also be chloroform, hexane and so forth.
- the following capillary columns may also be used in order to separate the component compounds: HP-1 made by Agilent Technologies Inc. (length 30 meters, bore 0.32 millimeter, film thickness 0.25 micrometers), Rtx-1 made by Restek Corporation (length 30 meters, bore 0.32 millimeter, film thickness 0.25 micrometers), and BP-1 made by SGE International Pty. Ltd. (length 30 meters, bore 0.32 millimeter, film thickness 0.25 micrometers).
- a capillary column CBP1-M50-025 (length 50 meters, bore 0.25 millimeter, film thickness 0.25 micrometers) made by Shimadzu Corporation may also be used for the purpose of avoiding an overlap of peaks of the compounds.
- the ratio of the liquid crystal compounds included in the composition may be calculated according to the following method.
- a mixture of the liquid crystal compounds is analyzed by gas chromatography (FID) .
- the ratio of peak areas in the gas chromatogram corresponds to the ratio of the liquid crystal compounds.
- the correction coefficient of respective liquid crystal compounds may be regarded as 1 (one). Accordingly, the ratio (percentage by weight) of the liquid crystal compounds can be calculated from the ratio of peak areas.
- the ratio of the compound to the mother liquid crystals was changed in the order of (10% by weight: 90% by weight), (5% by weight: 95% by weight) and (1% by weight: 99% by weight) .
- the values of the maximum temperature, the optical anisotropy, the viscosity and the dielectric anisotropy regarding the compound were obtained by means of this extrapolation method.
- the mother liquid crystals described below were used.
- the ratio of the component compounds were expressed as a percentage by weight. 17.2% 27.6% 20.7% 20.7% 13.8%
- Measurement methods The characteristics were measured according to the following methods. Most are methods described in the JEITA standards (JEITA-ED-2521B) which was deliberated and established by Japan Electronics and Information Technology Industries Association (abbreviated to JEITA), or the modified methods. No thin film transistors (TFT) were attached to a TN device used for measurement.
- JEITA-ED-2521B Japan Electronics and Information Technology Industries Association
- TFT thin film transistors
- composition in which compound (1) was not included was prepared.
- V-HB(2F,3F)-O2 (1-1) 8% 3-H2B(2F,3F)-O2 (1-3) 10% 3-BB(2F,3F)-O2 (1-5) 10% 2O-BB(2F,3F)-O2 (1-5) 3% 2-HHB(2F,3F)-O2 (1-7) 4% 3-HHB(2F,3F)-O2 (1-7) 7% V-HHB(2F,3F)-O2 (1-7) 5% 2-BB(2F,3F)B-3 (1-10) 10% 2-BB(2F,3F)B-4 (1-10) 10% 3-HDhB(2F,3F)-O2 (1-12) 6% 2-HBB(2F,3F)-O2 (1-14) 5% 3-HBB(2F,3F)-O2 (1-14) 6% 3-dhBB(2F,3F)-O2 (1-15) 4% 3-HH1OCro(7F,8F)-5 (1-20) 4% 3-HH-V (
- the flicker rate was in the range of 0.23% to 0.79%.
- the flicker rate of the device including the composition in Comparative Example 1 was 1.66%.
- the flicker rate in Examples fell into the range of 0% to 1% in this manner. It is thus concluded that the liquid crystal display device including the liquid crystal composition of the invention has excellent characteristics.
- the liquid crystal display device of the invention has characteristics such as a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, a long service life and a small flicker rate, and the flicker rate is in the range of 0% to 1%.
- this device can be used for a liquid crystal projector, a liquid crystal television and so forth.
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CN108239540B (zh) * | 2016-12-23 | 2022-02-25 | 江苏和成显示科技有限公司 | 液晶组合物及其显示器件 |
CN108239542A (zh) * | 2016-12-23 | 2018-07-03 | 江苏和成显示科技有限公司 | 具有负介电各向异性的液晶组合物及其显示器件 |
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JP2008134291A (ja) * | 2006-11-27 | 2008-06-12 | Epson Imaging Devices Corp | 液晶表示装置 |
JP2008139753A (ja) * | 2006-12-05 | 2008-06-19 | Epson Imaging Devices Corp | 液晶表示装置 |
JP2010123073A (ja) | 2008-11-21 | 2010-06-03 | Toshiba Corp | ページアクセス方法およびサーバ |
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TWI461512B (zh) | 2009-05-11 | 2014-11-21 | Jnc Corp | 液晶顯示元件 |
JP5013554B2 (ja) * | 2010-03-31 | 2012-08-29 | 株式会社ジャパンディスプレイセントラル | 液晶表示装置 |
EP2562233B1 (en) * | 2010-04-22 | 2019-07-17 | JNC Corporation | Liquid crystal composition and liquid crystal display element |
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KR101913996B1 (ko) * | 2010-10-04 | 2018-10-31 | 제이엔씨 주식회사 | 액정 조성물 및 액정 표시 소자 |
JP5636954B2 (ja) * | 2010-12-27 | 2014-12-10 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
JP2013195869A (ja) * | 2012-03-22 | 2013-09-30 | Japan Display West Co Ltd | 液晶表示装置、液晶表示装置の駆動方法、及び、電子機器 |
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KR20150013544A (ko) * | 2012-05-23 | 2015-02-05 | 제이엔씨 주식회사 | 액정 조성물 및 액정 표시 소자 |
US9150787B2 (en) | 2012-07-06 | 2015-10-06 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
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WO2014185122A1 (ja) * | 2013-05-15 | 2014-11-20 | シャープ株式会社 | 液晶表示装置 |
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EP3115437A1 (en) | 2017-01-11 |
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KR20160130980A (ko) | 2016-11-15 |
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